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Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes

2021Journal article Restricted access
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dc.contributor.authorGomes, Filipa Ramilo
dc.contributor.authorAddis, Yemataw
dc.contributor.authorTekamo, Israel
dc.contributor.authorCavaco, Isabel
dc.contributor.authorCampos, Débora L.
dc.contributor.authorPavan, Fernando R.
dc.contributor.authorGomes, Clara S.B.
dc.contributor.authorBrito, Vanessa
dc.contributor.authorSantos, Adriana O.
dc.contributor.authorDomingues, F.C.
dc.contributor.authorLuís, Ângelo
dc.contributor.authorMarques, M. Matilde
dc.contributor.authorPessoa, João Costa
dc.contributor.authorFerreira, Susana
dc.contributor.authorSilvestre, Samuel
dc.contributor.authorCorreia, Isabel
dc.date.accessioned2020-12-29T14:44:46Z
dc.date.available2020-12-29T14:44:46Z
dc.date.issued2021
dc.description.abstractSchiff bases (SB) obtained from S-methyl dithiocarbazate and aromatic aldehydes: salicylaldehyde (H2L1), o-vanillin (H2L2), pyridoxal (H2L3) and 2,6-diformyl-4-methylphenol (H3L4), and their corresponding Zn(II)-complexes (1-4), are synthesized. All compounds are characterized by elemental analyses, infrared, UV-Vis, nuclear magnetic resonance spectroscopy and mass spectrometry. The structures of H2L2 and [Zn2(L1)2(H2O)(DMF)] (1a) (DMF = dimethylformamide) are solved by single crystal X-ray diffraction. The SB coordinates the metal center through the Ophenolate, Nimine and Sthiolate atoms. The radical scavenging activity is tested using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with all ligand precursors showing IC50 values ~40 μM. Cytotoxicity studies with several tumor cell lines (PC-3, MCF-7 and Caco-2) as well as a non-tumoral cell line (NHDF) are reported. Interestingly, 1 has relevant and selective antiproliferative effect against Caco-2 cells (IC50 = 9.1 μM). Their antimicrobial activity is evaluated in five bacterial strains (Klebsiella pneumoniae, Acinetobacter baumannii, Listeria monocytogenes, Pseudomonas aeruginosa and Staphylococcus aureus) and two yeast strains (Candida albicans and Candida tropicalis) with some compounds showing bacteriostatic and fungicidal activity. The minimal inhibitory concentration (MIC90) of HnL against Mycobacterium tuberculosis is also reported, with H2L2 and H3L4 showing very high activity (MIC90 < 0.6 μg/mL). The ability of the compounds to bind bovine serum albumin (BSA) and DNA is evaluated for H3L4 and [Zn2(L4)(CH3COO)] (4), both showing high binding constants to BSA (ca. 106 M-1) and ability to bind DNA. Overall, the reported compounds show relevant antitumor and antimicrobial properties, our data indicating they may be promising compounds in several fields of medicinal chemistry.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.jinorgbio.2020.111331pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.6/10940
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relationCentro de Química Estrutural
dc.relationCentro de Química Estrutural
dc.relationFrom Drug Design to Chemical Toxicology: shaping predictive tools with Mass Spectrometry
dc.relationHealth Sciences Research Centre
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationApplied Molecular Biosciences Unit
dc.relationPRECISION ONCOLOGY BY INNOVATIVE THERAPIES AND TECHNOLOGIES
dc.relationAn epigenetic approach to anticancer therapy: Design, synthesis and biological evaluation of novel EZH2 inhibitors
dc.subjectSchiff basespt_PT
dc.subjectZn(II) complexespt_PT
dc.subjectS-methyl dithiocarbazatept_PT
dc.subjectS-methyl dithiocarbazatept_PT
dc.subjectAntimicrobialpt_PT
dc.subjectDNApt_PT
dc.titleAntimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleCentro de Química Estrutural
oaire.awardTitleFrom Drug Design to Chemical Toxicology: shaping predictive tools with Mass Spectrometry
oaire.awardTitleHealth Sciences Research Centre
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardTitlePRECISION ONCOLOGY BY INNOVATIVE THERAPIES AND TECHNOLOGIES
oaire.awardTitleAn epigenetic approach to anticancer therapy: Design, synthesis and biological evaluation of novel EZH2 inhibitors
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oaire.citation.startPage111331pt_PT
oaire.citation.titleJournal of Inorganic Biochemistrypt_PT
oaire.citation.volume216pt_PT
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person.familyNameSofia Figueiredo de Brito
person.familyNameOliveira dos Santos
person.familyNameDomingues
person.familyNameSantos Luís
person.familyNameFerreira
person.familyNameSilvestre
person.givenNameVanessa
person.givenNameAdriana
person.givenNameFernanda
person.givenNameÂngelo Filipe
person.givenNameSusana
person.givenNameSamuel
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project.funder.identifierhttp://doi.org/10.13039/501100001871
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rcaap.embargofctCopyright cedido à editora no momento da publicação.pt_PT
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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